S-methyl (2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butanethioate

Base Information

• Chemical Name: S-methyl (2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butanethioate
• CAS No.: 871514-33-9
• Molecular Formula: C₁₅H₂₀O₄S
• Molecular Weight: 296.387
• Mol file: 871514-33-9.mol

Synonyms:S-methyl (2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butanethioate

Chemical Property of S-methyl (2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butanethioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-methyl (2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butanethioate

There total 6 articles about S-methyl (2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butanethioate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

(4S,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carbonyl chloride + sodium thiomethoxide (5188-07-8) → S-methyl (2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butanethioate (871514-33-9)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; In dichloromethane; water; at 0 ℃; for 0.166667h;

DOI:10.1016/j.tet.2005.09.030

Reference yield: 23.0%

ethyl [2S,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate (871514-57-7) → ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate (191935-25-8) + S-methyl (2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butanethioate (871514-33-9)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 - -23 ℃;

DOI:10.1016/j.tet.2005.09.030

Reference yield:

(2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butyric acid (263711-17-7) + sodium thiomethoxide (5188-07-8) → S-methyl (2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butanethioate (871514-33-9)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; In dichloromethane; at 0 ℃;

DOI:10.1055/s-1997-6154

upstream raw materials:

(2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butyric acid

sodium thiomethoxide

ethyl [2S,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate

4-O-benzyl-2,3-O-isopropylidene-D-threose

Downstream raw materials:

(R,E)-4-(benzyloxy)methyl-5-[methylthio(trimethylsilyloxy)methylene]-2,2-dimethyl-1,3-dioxolane

(R,Z)-4-(benzyloxy)methyl-5-[methylthio(trimethylsilyloxy)methylene]-2,2-dimethyl-1,3-dioxolane

(1R,4S,8R)-8-Benzyloxymethyl-1-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-6,6-dimethyl-3-oxo-2,5,7-trioxa-spiro[3.4]octane-1-carboxylic acid ethyl ester

(1S,4S,8R)-8-Benzyloxymethyl-1-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-6,6-dimethyl-3-oxo-2,5,7-trioxa-spiro[3.4]octane-1-carboxylic acid ethyl ester